sugar-aza-crown ether | 1166264-09-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: sugar-aza-crown ether
• 英文别名: SAC；(1R,6R,7S,11R,12R,17R,18S,22R)-9,9,20,20-tetramethyl-8,10,19,21,23,24-hexaoxa-3,14-diazapentacyclo[15.5.1.16,12.07,11.018,22]tetracosane
• CAS: 1166264-09-0
• 化学式: C₂₀H₃₄N₂O₆
• 分子量: 398.5
• InChiKey: MTQFUJQDSJBNRV-BXYRDPEGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  28
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  79.4
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  sugar-aza-crown ether 、 1-氯甲基芘 在 四丁基碘化铵 、 potassium carbonate 、 potassium iodide 作用下， 以 乙腈 为溶剂， 以0.26 g的产率得到(1R,6R,7S,11R,12R,17R,18S,22R)-9,9,20,20-tetramethyl-3,14-bis(pyren-1-ylmethyl)-8,10,19,21,23,24-hexaoxa-3,14-diazapentacyclo[15.5.1.16,12.07,11.018,22]tetracosane
  参考文献：
  名称：

  A sugar-aza-crown ether-based fluorescent sensor for Cu2+ and Hg2+ ions

  摘要：

  A sugar-aza-crown ether (SAC)-based fluorescent sensor 4 was prepared. It contains a pyrene as the fluorophore and its fluoroionophoric properties toward transition metal ions were investigated. Chemosensor 4 exhibits highly selective recognition toward Cu2+ and Hg2+ ions among a series of tested metal ions in methanol solution. The association constants for 4*Cu2+ and 4*Hg2+ in methanol solution were calculated to be 7.4 x 10(1) M-1 and 4.4 x 10(3) M-1, respectively. Chemosensor 4 formed complexes with the Cu2+ or Hg2+ ion at a 1:1 ligand-to-metal ratio with a detection limit of 1.3 x 10(-4) M Cu2+ and 1.26 x 10(-5) M Hg2+, respectively. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.03.010
• 作为产物：
  描述：

  methyl 2-C-(5-azido-5-deoxy-2,3-di-O-isopropylidene-α-D-ribofuranosyl)acetaldehyde 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以80%的产率得到sugar-aza-crown ether
  参考文献：
  名称：

  通过还原胺化/酰胺化从C-核糖基叠氮基醛合成呋喃糖-糖氮杂-冠醚的简便方法

  摘要：

  通过一锅还原α-异头异构体C-核糖基叠氮基醛的胺化反应，开发了一种短而高效的途径制备呋喃糖-氮杂-冠冕醚的α-异头物。另外，通过酰胺化由线性二糖前体合成β-端基呋喃糖-氮杂-冠醚，然后进行微波辅助酰胺还原。

  DOI：

  10.1016/j.carres.2009.03.008

文献信息

• Convenient approaches to synthesis of furanoid sugar-aza-crown ethers from C-ribosyl azido aldehyde via a reductive amination/amidation
  作者：Yu-Chi Hsieh、Jiun-Ly Chir、Wei Zou、Hsiu-Han Wu、An-Tai Wu

  DOI：10.1016/j.carres.2009.03.008

  日期：2009.5

  alpha-anomer of a furanoid sugar-aza-crown ether was developed by a one-pot reductive amination of an alpha-anomer C-ribosyl azido aldehyde. In addition, the beta-anomer furanoid sugar-aza-crown ether was synthesized from a linear disaccharide precursor via amidation and then followed by microwave-assisted amide reduction.

  通过一锅还原α-异头异构体C-核糖基叠氮基醛的胺化反应，开发了一种短而高效的途径制备呋喃糖-氮杂-冠冕醚的α-异头物。另外，通过酰胺化由线性二糖前体合成β-端基呋喃糖-氮杂-冠醚，然后进行微波辅助酰胺还原。
• A sugar-aza-crown ether-based fluorescent sensor for Hg2+ and Cu2+
  作者：Yu-Chi Hsieh、Jiun-Ly Chir、Hsiu-Han Wu、Po-Sheng Chang、An-Tai Wu

  DOI：10.1016/j.carres.2009.08.027

  日期：2009.11

  A fluorescent sensor, 5, based upon the sugar-aza-crown ether structure with two anthracenetriazolymethyl groups was prepared and its fluoroionophoric properties toward transition metal ions were investigated. In methanol, the sensor exhibits highly selective recognition of Cu2+ and Hg2+ ions among a series of tested metal ions. The association constant for 5 center dot Cu2+ and 5 center dot Hg2+ in methanol was calculated to be 4.0 x 10(5) M-1 and 1.1 x 10(5) M-1, respectively. The detection limits for the sensing of Cu2+ and Hg2+ ions were 1.39 x 10(-6) M and 1.39 x 10(-5) M, respectively. (C) 2009 Elsevier Ltd. All rights reserved.
• A sugar-aza-crown ether-based fluorescent sensor for Cu2+ and Hg2+ ions
  作者：Yu-Chi Hsieh、Jiun-Ly Chir、Shih-Tse Yang、Shau-Jiun Chen、Ching-Han Hu、An-Tai Wu

  DOI：10.1016/j.carres.2011.03.010

  日期：2011.5

  A sugar-aza-crown ether (SAC)-based fluorescent sensor 4 was prepared. It contains a pyrene as the fluorophore and its fluoroionophoric properties toward transition metal ions were investigated. Chemosensor 4 exhibits highly selective recognition toward Cu2+ and Hg2+ ions among a series of tested metal ions in methanol solution. The association constants for 4*Cu2+ and 4*Hg2+ in methanol solution were calculated to be 7.4 x 10(1) M-1 and 4.4 x 10(3) M-1, respectively. Chemosensor 4 formed complexes with the Cu2+ or Hg2+ ion at a 1:1 ligand-to-metal ratio with a detection limit of 1.3 x 10(-4) M Cu2+ and 1.26 x 10(-5) M Hg2+, respectively. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis of a sugar-aza-crown ether-based cavitand as a selective fluorescent chemosensor for Cu2+ ion
  作者：Yu-Chi Hsieh、Jiun-Ly Chir、Hsiu-Han Wu、Chao-QI Guo、An-Tai Wu

  DOI：10.1016/j.tetlet.2009.10.093

  日期：2010.1

  A chemosensor based upon the sugar-aza-crown ether 7 with one anthracenetriazolymethyl moiety was prepared and its fluoroionophoric properties toward transition metal ions were investigated. Chemosensor 7 exhibits highly selective recognition toward Cu2+ ion among a series of tested metal ions in MeOH solution. The association constant for 7*Cu2+ in MeOH solution was calculated to be 2.5 x 10(4) M-1. (C) 2009 Elsevier Ltd. All rights reserved.